Have You Ever Sabotaged a Date That You Knew Was Doomed?

The other day, a guy came up to my friend Kathryn in a restaurant. He said his friends made him come over because he’d been watching her during dinner. He wanted to know if she’d go out with him. Kathryn said, “Based on what?” Ha! His answer was that they had ordered the same thing.

He was relatively cute so she gave him her number, but afterwards had to try to get him to tell her anything about him via text message—just the basic details like age, career, etc. She felt it was strange not knowing anything about him.

Well, Kathryn, brave as she was, met him a few days later for “just a normal awkward date at a wine bar.” He was 5 years younger and they had zero chemistry. They didn’t have the same sense of humor and they didn't have anything in common. And he wasn’t very smart.

You’re boring but I guess you can look at my cleavage.

So she did something that was unlike her. Kathryn started saying all these negative things about herself, her former roommate, and she even mentioned an ex. “It was stuff I probably wouldn't have lead with otherwise,” she says “and the stuff made me sound like a high-maintenance crazy person.”

Was she subconsciously trying to make herself unattractive to him? I have totally done this on a bad date. I got lazy and I wasn’t on my best behavior. But apparently her self-sabotage didn’t work, because he emailed her the next day.

It seems like those virtual stranger dates rarely work out. I went out with a waiter once that I didn’t know—it was a nightmare.

Have you ever been picked up randomly? Did it work out with the guy? Do you sabotage bad dates by doing things that turn off men?